Accession Number:

AD0600223

Title:

ADDITION AND DISPLACEMENT REACTIONS WITH UNSATURATED HYDROCARBONS.

Descriptive Note:

Rept. for 1 Sep 62-31 Aug 63,

Corporate Author:

WISCONSIN UNIV MADISON

Personal Author(s):

• Goering,Harlan L.

Report Date:

1964-04-14

Pagination or Media Count:

20.0

Abstract:

The cuprous-bromide-catalyzed reaction of t-butyl perbenzoate and bicyclo-3.2.1-octene-2 I results in the formation of exoaxial -bicyclo-3.2.1-oct-3-en-2-yl benzoate IIIa which contains 1 of the endo isomer. Optically active I gives racemic IIIa which means that the allylic carbon atoms C2 and C4 are completely randomized. These results are consistent with the Kochi mechanism i.e., abstraction of an allylic hydrogen atom to give the symmetrical bicyclo3.2.1oct-3en2-yl radical II which is stereoselectively converted to racemic exo benzoate IIIa. Progress is also reported of studies concerning the solvolysis of alpha-p-anisylethyl p-nitrobenzoate ROCOC6H4NO2 under various conditions. Author

Descriptors:

• (*BENZOATES
• STEREOCHEMISTRY)
• (*BENZOATES
• CHEMICAL REACTIONS)
• (*STEREOCHEMISTRY
• BENZOATES)
• HYDROCARBONS
• MOLECULAR ISOMERISM
• MOLECULAR ROTATION
• COPPER COMPOUNDS
• BROMIDES
• NITROBENZENES
• IONIZATION
• ACETONES

Subject Categories:

Distribution Statement:

APPROVED FOR PUBLIC RELEASE